DAY 1 - Wednesday October 11

Arrive in Onomichi

Welcome to Onomichi! This fascinating port town is the gateway to the Shimanami Kaido Islands and Bridges Cycle Route. Easily accessed by bullet train or local train, our beautiful cycling-themed hotel is located on the wharf, just a 5-minute walk from the station.

Will and Robbie will introduce the team and answer any questions. We’ll help set up your bikes and ensure everything is running smoothly. Let’s pop out for a short shake-down ride.

My guess is that you won’t lose any weight on this trip. Japanese cuisine offers a great variety of fresh seafood, meats, and vegetarian dishes. Many of our hotels provide buffet-style breakfasts and dinners, allowing you to try a range of local flavours. Yes, you will eat well.

Let’s raise a glass (Sake) to the adventure ahead.

/ Accommodation: Onomichi U2

Ps, our guides are based in Matsuyama, where there are daily flights from Tokyo. You are welcome to meet us there and we’ll drive you to Onomichi. We can also help with extra accommodation for those arriving early.

PPS, a quick note about the weather. Mid-to-late October is an ideal time for cycling in Japan. Expect daytime temperatures between 20–25°C, with cooler evenings around 15°C. Autumn colours will be starting to show, especially in the mountains, making for some stunning rides.

/ Meals included: Dinner

DAY 2 - Thursday October 12

Onomichi to Yugeshima Island – Shimanami Kaido Cycling

After breakfast, we’ll jump onto our bikes and ride hotel to hotel. It’s not a massive ride at only 55km (400VM) but it’s a great way of starting our cycling holiday. A very short ferry ride gets us to the start of the Shimanami Kaido.

Today is a stunning ride on one of the best cycling routes in the world! We’ll explore the islands, jumping off the beaten path to visit a local shrine and soak in the views.

We’ve organised a picnic lunch. This could be onigiri, a bento box, or perhaps some delicious Japanese breads and pastries from one of the local bakeries. Sounds terrible.

Our destination for the night is Ikuchi Island, famous for its citrus groves and cycling-friendly roads. After arriving, you’ll have time to unwind in the hotel’s beautiful spa before we enjoy a well-earned dinner featuring fresh local seafood and produce.

Team Macchiato: While the cyclists are out conquering the Shimanami Kaido, Team Mac enjoy a morning temple walk through the fascinating old streets and alleyways of Onomichi and visit the stunning Senko-ji Temple observatory for fantastic views of the town and the Inland Sea. After lunch in Onomichi, hop into the van and head to the islands, stopping at Shirataki-yama, a mountain viewpoint offering 360-degree views of the islands and bridges. From there you’ll make your way to Setoda on Ikuchi Island, where you’ll have time to relax at the hotel’s spa or explore the old shopping arcade of this charming fishing village.

/ Accommodation: Inland Sea Resort FESPA
/ Meals included: Breakfast, Lunch & Dinner

DAY 3 - Friday October 13

Yugeshima Island to Saijo

Yesterday was fantastic. Let’s do it all again today. Rinse, rinse and repeat. We increase the mileage slightly today. 75km and 600vm.

Japan’s roads are smooth, well-maintained, and often have little traffic—perfect for cycling. Climbs are well-graded, downhills are fun and flowing, and drivers are very courteous.

Another breath-taking ride takes us across beautifully engineered bridges, each offering spectacular views of the Seto Inland Sea and its scattered islands. We’ll also visit Oyamazumi Shrine, one of the region’s most ancient and significant shrines, steeped in samurai history.

We’ll finish the ride cycling over the 4km long Kurushima suspension bridge and onto Shikoku Island. A short transfer to our accommodation, which features a rooftop hot spring—the perfect way to relax and recover while taking in mountain and sea views.

Team Macchiato: While the cyclists are out riding the Shimanami Kaido, Team Mac will have a few optional activities to choose from. They can join a guided citrus farm tour on Ikuchi Island, where they’ll learn about the island’s famous citrus groves and sample some fresh produce. Alternatively, they can take a short cruise near the Tatara Bridge for a different perspective of the Inland Sea. Afterward, they’ll continue their journey toward Shikoku, stopping at some fascinating spots along the way.

/ Accommodation: Saijo Hotel
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

Ps, fingers crossed. The 2026 trip was perfectly timed around the Isono Shrine Festival. Let’s hope that happens in 2028. The most famous part of Saijo Matsuri, featuring dozens of elaborately decorated danjiri floats and mikoshi.

DAY 4 - Saturday October 14

Saijo to Uchiko – UFO Line & Mt. Ishizuchi

Today’s ride is a big one, but it’s also one of the most rewarding. 115km and 1500m of climbing. Yes, we’ll have a latte and cappuccino plan for those not wanting to ride the whole distance. Today we tackle the UFO Line, a stunning route that winds its way up Mt. Ishizuchi, the highest peak in western Japan. The panoramic views stretch across rugged mountain ranges to the Pacific coast—it’s worth every pedal stroke.

Climb stats...

• UFO Line: 27 km
• UFO Line elevation: approximately 1,300m
• UFO Line high point: approximately 1,690m

Ouch...

After the epic climb and exhilarating descent, we’ll stop for lunch in Omogo Gorge, known for its crystal-clear waters and dramatic rock formations. From there, we’ll ride through emerald-green river valleys, passing small villages and pristine countryside as we make our way to Uchiko. A hidden gem, famous for its well-preserved historical district and charming old merchant houses. It’s like stepping back in time to a quieter, more traditional Japan.

Team Macchiato: Team Mac head to Matsuyama City, Shikoku’s largest city. Here, they’ll visit Matsuyama Castle (optional entry) and take in the city’s rich history and culture. They’ll also stop at a local dyeing shop, where they can try their hand at indigo dyeing—a fun and unique experience. After lunch in the city, they’ll make their way to Uchiko to reunite with the cyclists and enjoy a wonderful group dinner.

/ Accommodation: Uchiko - Inns of Uchiko
/ Meals included: Breakfast, Lunch & Dinner

Ps, yes – we’ll have shorter ride options available today.

DAY 5 - Sunday October 15

Uchiko – Rest Day

Shall we call it an active rest day. There’s still a 30km coffee ride on offer.

Speaking of coffee? Naru Cafe (なるカフェ) is a restored kominka (traditional Japanese farmhouse) café in Uchiko, Ehime, located beside the historic Main Haga Family Residence. Housed in a building that is more than 100 years old, it combines a retro-modern interior with handmade sweets, specialty coffee, and light meals, making it a popular stop while exploring Uchiko's preserved historic streets. 

Today is all about slowing down and soaking in the charm of Uchiko. We’re staying in traditional houses within the historic district, beautifully refurbished into modern Japanese style accommodation. Think sliding paper doors, tatami mats, and a serene atmosphere— it’s the perfect place to feel at home away from home.

Whether you choose to explore or simply relax and unwind, today is all about enjoying the laid-back vibe of this lovely town. There are some optional excursions which we are happy to arrange. Perhaps a visit to a historic paper mill, where they produce stunning Japanese washi paper?

Early evening, we’ll regroup for a sake tasting. Sake is Japan’s iconic rice wine, and Uchiko is the perfect place to try it. You’ll then be free to head into town to dine at one of the many local restaurants.

/ Accommodation: Uchiko - Inns of Uchiko
/ Meals included: Breakfast (Lunch & Dinner are own arrangements)

DAY 6 - Monday October 16

Uchiko to Uwajima – Uwa Kai Coastal Riding

After a short drive south to the town of Uwa, we’ll continue our Shikoku adventure with a ride to the port town of Uwajima. Today’s route is challenging (75km but almost 1k in climbing) but incredibly rewarding, with stunning views of the Uwa Sea and terraced orange orchards clinging to the hillsides. It’s Shikoku at its most beautiful.

Uwajima is a lively port town with a rich history and a laid-back feel. After arriving, you’ll have time to explore before we gather for a sunset happy hour (weather permitting) and another delicious dinner featuring fresh local seafood.

Our hotel is quite large with 82 rooms. Including Western-style and Japanese-style options, with some rooms providing views towards Uwajima Castle. One of only twelve original castle keeps remaining in Japan and an important cultural landmark of Ehime. Built by renowned castle architect Todo Takatora and later associated with the Date clan, the castle sits on a wooded hilltop overlooking Uwajima and the bay.

Team Macchiato: Team Mac visit nearby Ozu City. They’ll take a stroll through the old streets and enjoy an optional river cruise on a traditional boat. Afterward, they’ll head to the Uwa Sea to visit Doi Shunju, a pearl jewellery workshop, where they can learn about the art of pearl cultivation and even pick up a unique souvenir. They’ll then make their way to Uwajima to reunite with the cyclists for sunset happy hour and dinner.

/ Accommodation: JR Hotel Clement Uwajima
/ Meals included: Breakfast, Lunch & Dinner

DAY 7 - Tuesday October 17

Uwajima to Cape Ashizuri – Queen stage 

It’s our queen stage. Door to door is 130km and 1500VM. It’s also the most spectacular ride of the trip. We head inland and make our way down to Cape Ashizuri, where the Uwa Sea meets the Pacific Ocean. This is Shikoku’s rugged southern tip, and it’s as dramatic as it sounds.

The route takes us through rolling hills, quiet countryside, and along coastal roads with jaw dropping views. Cape Ashizuri itself is wild, remote, and incredibly beautiful. After arriving, you’ll have time to explore the area, including the iconic Ashizuri Lighthouse and Kongofukuji Temple, one of the 88 temples on the Shikoku Pilgrimage.

Swimming? I thought this sounded really warm but surely google can’t be wrong. (No doubt you’ll tell me.) The Pacific Ocean around Tosashimizu remains pleasantly warm in October, with sea temperatures averaging around 25–26°C. The water is generally warm enough for swimming and water activities, although temperatures gradually become cooler towards the end of the month.

Team Macchiato: While the cyclists are out tackling the ride to Cape Ashizuri, Team Mac will start their day with a morning stroll through the beautiful Nanrakuen Japanese Gardens. They’ll then visit the Satoumi Aquarium, where they can learn about the unique marine life of the Uwa Sea. Afterward, they’ll travel to Cape Ashizuri, where they’ll explore the lighthouse, take a scenic coastal walk, and visit Kongofuku-ji Temple. They’ll reunite with the cyclists at the accommodation for a well-deserved dinner.

/ Accommodation: The Mana Village
/ Meals Included: Breakfast, Lunch & Dinner

DAY 8 - Wednesday October 18

Pacific Coast & Shimanto River

We leave the rugged beauty of Cape Ashizuri and follow the Pacific coast north towards Shimanto. It’s a beautiful coastal ride, with plenty of ocean views as we make our way towards the mighty Shimanto River. Navigation wise – pretty easy. Keep the blue stuff to the right and the green stuff to the left. What are the chances we’ll lose someone... Hmm.

The main course for today is 55km and 400vm. Followed by an optional dessert of a 30km river loop. (Highly recommended.) My Upper Hutt maths tells me that’s a total of 85km and 700vm. I’m sure the team can find an extra 15km for those wanting to crack the ton.

The undisputed gem for today is the Shimanto river. It is one of Japan’s great untouched rivers, winding through the mountains and rural communities of southern Shikoku before reaching the Pacific. Known as Japan’s last clear stream. It’s 196km length makes it the longest river in Shikoku.

We’ll finish the day at our beautiful accommodation on the coast. Shimanto no Yado is a peaceful riverside hotel set in the natural surroundings of the Shimanto area in Kochi Prefecture. The hotel provides a relaxing base from which to enjoy the region’s beautiful rural scenery and traditional culture.

Team Macchiato: While the cyclists are out riding along the Shimanto River, Team Mac will visit Nakamura Town. Here, they’ll have the option to hire a Japanese shopping bike (mamachari) and take an easy cycle along the river to one of the iconic submersible bridges. After lunch at a local restaurant, they’ll make their way to Shimanto to reunite with the cyclists for dinner.

/ Accommodation: Shimanto no Yado
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

Day 9 - Thursday October 19

Shimanto to Tosa-Kure

Today, we continue following the Shimanto River to its source, then head over the hills and back to the Pacific coast. It’s a mix of river valleys, forested climbs, and coastal roads, with plenty of stunning views along the way. Cycle Distance: 60- 95km with very little elevation gain.

Our destination for the night is Tosa-Kure, a small coastal town famous for its fishing industry and fresh seafood.

Team Macchiato: While the cyclists are out riding to Tosa-Kure, Team Mac will visit a beautiful local gorge for a scenic morning walk. In the afternoon, you leave the van for a scenic train ride on the Yodo Sen Line to Kubokawa before catching back up with the cyclists.

Tonight’s hotel is the most traditional on this trip. A true Japanese ryokan (旅館) is a type of Japanese inn that offers an authentic cultural experience, often centred around relaxation, hospitality, and traditional aesthetics.

Key Features of a traditional ryokan:

1. Tatami Rooms: Floors are covered with tatami mats (woven straw). You’ll sleep on a futon (foldable mattress) laid out at night.
2. Kaiseki Cuisine: A multi-course traditional Japanese dinner, often featuring seasonal and local ingredients. Usually served in your room or in a private dining area.
3. Onsen (Hot Spring Baths): Many ryokans are located near natural onsen and include communal or private baths. Bathing etiquette is important (e.g. wash before entering the bath, no clothing/swimsuits).
4. Yukata: A casual cotton kimono provided to wear during your stay. Many guests wear it to dinner and around the ryokan.
5. Omotenashi (Hospitality): Deeply rooted in Japanese hospitality, staff often greet you with tea and are attentive but unobtrusive.

Tonight we are really going to encourage you to wear your kimono to dinner. When in Japan!!

/ Accommodation: Kuroshio Honjin
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

DAY 10 - Friday October 20

Pacific Coast to Kochi City

We follow the Pacific coast towards Kochi City, the lively capital of Kochi Prefecture. The ride is a mix of coastal roads, rolling hills and a few challenging climbs before we arrive in the city.

A relatively short day which is good timing as we start to look forward to Sunday’s event. Only 65km and 800m of climbing. We’ll probably start a bit later today to give you a sleep in.

Given that it’s pretty gentle we would encourage you to stop and take photos. There’s a coffee spot at 15km and the Otonashi Shrine at 25km is an absolute must see. It’s known locally as a place to pray for good relationships and marriage.

For the record – we’ve had 2 RH marriages. Maybe a 3rd?

Kochi's trams are still running through the city, making it possible to see a modern Japanese city while riding a very old-school electric streetcar.

Tonight is a free evening to explore Kochi at your own pace. You might want to check out the famous Hirome Market, a lively night market filled with local eateries serving everything from fresh sushi to grilled seafood.

Team Macchiato: Team Mac will have time in the morning to explore the small seaside town of Kure. They’ll then follow the cyclists’ route, stopping at highlight points along the way. They’ll arrive early in Kochi City to explore the markets and shops before reuniting with the cyclists for the evening.

/ Accommodation:  Sansuien
/ Meals Included: Breakfast (Lunch & Dinner are own arrangements)

DAY 11 - Saturday October 21

Optional 40km??

It’s a semi rest day as we look forward to tomorrow’s big day. Certainly, those doing the 145km should be in preparation mode.

After breakfast, we visit Kochi Castle, one of Japan’s few original castles to have survived since the Edo period. The castle grounds offer great views across the city and surrounding mountains.

After our castle visit, we’ll drive to Imabari, the gateway to the Shimanami Kaido. The journey takes around two hours, so sit back, relax and enjoy the scenery. Upon arrival, you can opt in or out of the very relaxed 40km city ride.

Totally up to you if you ride or not. Our Shimanami Prime Hotel is pretty much brand new – opened in 2024. It’s conveniently located right in the heart of Imabari and the top-floor offers a public bath and sauna, providing views across the sea, and the Shimanami Kaido.

Pre-Event Registration & Expo

Our Japanese team on the ground will take care of the event registration for everyone, so there is no need to register individually.

We dine together at a local yakitori restaurant, specialising in Imabari-style grilled chicken. Unlike traditional yakitori, Imabari yakitori is typically cooked on a hot iron plate rather than over charcoal. The chicken is pressed against the plate as it cooks, creating a delicious crispy exterior, and is served alongside a variety of other grilled dishes.

/ Accommodation: Shimanami Prime Hotel Imabari
/ Meals Included: Breakfast, Dinner

DAY 12 - Sunday October 22

Cycle Shimanami Event

The highlight of the trip and the reason we are in Japan. The whole itinerary was based around today. Japan’s largest cycling event. Held every 2 years.

This iconic ride takes us back onto the Shimanami Kaido, but this time with the unique opportunity to ride sections of the expressway completely closed to traffic, alongside thousands of cyclists from Japan and around the world.

There are 3 distances to choose from. 70km, 100km or 145km. Whatever your choice – you are in for a cracking day. Riding across the spectacular bridges and islands of the Seto Inland Sea. With closed roads, incredible views and cyclists everywhere, it promises to be a memorable finale to our time on the bike.

Our team will have a plan for after you all finish. If it’s like the other sportives we ride, then no doubt there will be a nice park for you to relax in and catch up with everyone.

Team Macchiato: While the cyclists take on the Cycle Shimanami Event, Team Mac will head into town for a Japanese cooking lesson. They’ll learn how to prepare traditional dishes and enjoy the fruits of their labour for lunch. Afterward, they’ll visit the Imabari Towel Museum to learn about the history of this unique industry. They’ll reunite with the cyclists in the evening for the final group dinner.

Tonight, we regroup and celebrate our final dinner together. What a fantastic journey it has been.

Thank you for being awesome.

/ Accommodation: Shimanami Prime Hotel Imabari
/ Meals Included: Breakfast, Lunch, Dinner

DAY 13 - Monday October 23

Farewell

Today, we say our goodbyes and head our separate ways. Whether you’re flying home or continuing your travels in Japan, we hope you leave with unforgettable memories, new friends and a deep appreciation for the beauty of this incredible country.

We are aware that some of you have flights booked from Matsuyama. We’ll depart the hotel at about 9.30am and have you at the airport by 11am.

On behalf of Ride Holidays – Thank You. We really appreciate your loyalty.

Safe travels home,
Karl, Robbie and the We Ride Japan team

/ Meals Included: Breakfast